Acetic Acid → 1-(N-tert-butyloxycarbonyl-pyrrolidin-3-ylmethyl)-6-nitro-2,3-dihydroindole

HRID 376252

Reaction equation

HRID 376252 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[N+:29]([C:32]1[CH:40]=[C:39]2[C:35]([CH2:36][CH2:37][NH:38]2)=[CH:34][CH:33]=1)([O-:31])=[O:30].C(O)(=O)C>ClCCl.C(OCC)(=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH:24]([CH2:27][N:38]2[C:39]3[C:35](=[CH:34][CH:33]=[C:32]([N+:29]([O-:31])=[O:30])[CH:40]=3)[CH2:36][CH2:37]2)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 297576-NitroindolineHCID 4692112(+-)-1-(tert-Butoxycarbonyl)pyrrolidine-3-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 109369451-(N-tert-butyloxycarbonyl-pyrrolidin-3-ylmethyl)-6-nitro-2,3-dihydroindole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

91.5 mmol (19.4 g) of solid sodium triacetoxyborohydride are added slowly, at 20° C., to a solution of 60.8 mmol (12.1 g) of 1-(tert-butyloxycarbonyl)-3-formylpyrrolidine, 60.8 mmol (10 g) of 6-nitroindoline and 60.8 mmol (3.65 g) of acetic acid in 100 ml of dichloromethane. After 2 hours' stirring, the reaction mixture is diluted with ethyl acetate. The organic phase is washed with water until pH=8, and the aqueous phase is then extracted with dichloromethane. After removal of the solvent by evaporation, the expected product is obtained.

Workup

  1. washThe organic phase is washed with water until pH=8
  2. extractionthe aqueous phase is then extracted with dichloromethane
  3. customAfter removal of the solvent
  4. customby evaporation

Sources & evidence

ORD record
ord-d075277b233c45d7906be90b26a3d538
Source dataset
uspto-grants-2000_02
Patent number
US06020336

Linked notes

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